2,9,10-trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-1-ol

Base Information

• Chemical Name: 2,9,10-trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-1-ol
• CAS No.: 5083-88-5
• Molecular Formula: C20H23 N O4
• Molecular Weight: 341.407
• Hs Code.: 2933990090
• NSC Number: 310621
• Nikkaji Number: J3.170.279H
• Wikidata: Q104250224
• Mol file: 5083-88-5.mol

Synonyms:thaliporphine;thaliporphine hydrochloride

Chemical Property of 2,9,10-trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-1-ol

Chemical Property:

• Vapor Pressure: 7.51E-11mmHg at 25°C
• Boiling Point: 505.7°C at 760 mmHg
• PKA: 9.58±0.20(Predicted)
• Flash Point: 259.7°C
• PSA: 51.16000
• Density: 1.222g/cm³
• LogP: 3.10800
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 341.16270821
• Heavy Atom Count: 25
• Complexity: 475

Purity/Quality:

99% ^*data from raw suppliers

Thaliporphine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=CC(=C(C3=C2C1CC4=CC(=C(C=C43)OC)OC)O)OC

Technology Process of 2,9,10-trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-1-ol

There total 6 articles about 2,9,10-trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-1-ol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 63.0%

glaucine (475-81-0) → isoboldine (3019-51-0,5164-93-2,13529-67-4,104597-61-7) + bracteoline (25651-04-1) + 11-sulfonyl-1,11-anhydrobracteoline (1418137-71-9) + thaliporphine (5083-88-5,20068-96-6)

Guidance literature:

With sulfuric acid; In water; at 20 ℃; for 312h;

DOI:10.1021/np3007765

Reference yield:

N-formyl-laurolitsine (371196-15-5) → isoboldine (3019-51-0,5164-93-2,13529-67-4,104597-61-7) + bracteoline (25651-04-1) + 11-sulfonyl-1,11-anhydrobracteoline (1418137-71-9) + thaliporphine (5083-88-5,20068-96-6)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate / methanol / 24 h / 70 °C

2: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere; Reflux

3: sulfuric acid / water / 312 h / 20 °C

With lithium aluminium tetrahydride; sulfuric acid; potassium carbonate; In tetrahydrofuran; methanol; water;

DOI:10.1021/np3007765

Reference yield:

(+)-norboldine (5890-18-6,568-39-8) → isoboldine (3019-51-0,5164-93-2,13529-67-4,104597-61-7) + bracteoline (25651-04-1) + 11-sulfonyl-1,11-anhydrobracteoline (1418137-71-9) + thaliporphine (5083-88-5,20068-96-6)

Guidance literature:

Multi-step reaction with 4 steps

1: N,N-dimethyl-formamide / 60 h / 90 °C / Sealed tube

2: potassium carbonate / methanol / 24 h / 70 °C

3: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere; Reflux

4: sulfuric acid / water / 312 h / 20 °C

With lithium aluminium tetrahydride; sulfuric acid; potassium carbonate; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;

DOI:10.1021/np3007765

upstream raw materials:

O-acetylthaliporphine

glaucine

N-formyl-laurolitsine

(+)-norboldine

Refernces

Aporphine synthesis by Pschorr cyclization of aminophenols. An improved synthesis of a thalicarpine precursor.

10.1021/jo00942a048

The research presents an improved general synthesis of aporphines via Pschorr cyclization of 1-(2’-aminobenzyl)-7-hydroxy-l,2,3,4-tetrahydroisoquinolines. The key chemicals involved in this research include o-nitrotoluenes (2a-e), 6-methoxy-7-hydroxy-3,4-dihydroisoquinolinium methiodide, KO-t-Bu, Pd/C, Zn-H2SO4, diazomethane, and copper powder. The synthesis involves several steps: condensation of o-nitrotoluenes with 6-methoxy-7-hydroxy-3,4-dihydroisoquinolinium methiodide in the presence of KO-t-Bu to form 1-(2’-nitrobenzyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinolines (3a-e); reduction of these compounds with Pd/C or Zn-H2SO4 to obtain aminophenols (4a-f); and cyclization of the aminophenols to form 1-hydroxyaporphines (5a-f) using diazotization and copper powder. The final products include thalicmidine (5g), nuciferine (6a), glaucine (6g), and the thalicarpine precursor 6e. The synthesis is notable for achieving the highest yields reported to date for these compounds.

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